US561276A - Alcide frangois poirrier - Google Patents
Alcide frangois poirrier Download PDFInfo
- Publication number
- US561276A US561276A US561276DA US561276A US 561276 A US561276 A US 561276A US 561276D A US561276D A US 561276DA US 561276 A US561276 A US 561276A
- Authority
- US
- United States
- Prior art keywords
- coloring
- sulfur
- matters
- brown
- alkaline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- OSVXSBDYLRYLIG-UHFFFAOYSA-N Chlorine dioxide Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 title description 4
- 241000272194 Ciconiiformes Species 0.000 title description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 30
- 229910052717 sulfur Inorganic materials 0.000 description 30
- 239000011593 sulfur Substances 0.000 description 30
- 239000000975 dye Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229920000742 Cotton Polymers 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 8
- PXUQTDZNOHRWLI-QOPOCTTISA-O Primulin Natural products O(C)c1c(O)c(OC)cc(-c2c(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)cc3c(O)cc(O)cc3[o+]2)c1 PXUQTDZNOHRWLI-QOPOCTTISA-O 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 150000003464 sulfur compounds Chemical class 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Adhd patch Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 2
- 229940060942 Methylin Drugs 0.000 description 2
- CHMBIJAOCISYEW-UHFFFAOYSA-N N-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 2
- XSCFKJGIAYKLRV-UHFFFAOYSA-N N-naphthalen-1-ylnitramide Chemical compound C1=CC=C2C(N[N+](=O)[O-])=CC=CC2=C1 XSCFKJGIAYKLRV-UHFFFAOYSA-N 0.000 description 2
- 229940079877 Pyrogallol Drugs 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
Definitions
- Example I I heat to 200 to 250 centigrade for three hours one hundred kilos acetyl-paraphenylenediamin and two hundred kilos sulfur. There shortly occurs a Violent reaction and evolution of sulfureted hydrogen, on the cessation of which the material is left to cool. The coloring-matter obtained is soluble in hot alkaline sulfids, and in this condition directly dyes cotton a brown yellow.
- Example II I heat to about 300 centigrade for three to four hours one hundred kilos diacetyldiazobenzidin, one hundred kilos dry sodium sulfite, and two hundred kilos sulfur. Then the reaction is complete, the material is allowed to cool and can in this conditon be applied to use.
- the coloring-matter which is readily soluble in water, dyes cotton yellow.
- Analogous coloring-matters may be prepared by heating under like conditions acetylparanitranilin, the nitrotoluidins and nitroalpha-naphthylamin, acetylated, or the corresponding amido derivatives. All these coloring-matters have the same properties. They are soluble in water, in alkaline sulfids, sulfites, and bisulfites, insoluble in acids. It is known, on the other hand, that the primulins and dehyrothiotoluidins or Xylidins are basic bodies insoluble in alkalies.
- alkaline bisulfites has little stability, and even at 100 centigrade it reproduces the primary material.
- the solutions in alkaline sulfids are brown, thus differing essentially from cachou de laval and also from the coloring matters of the United States patents mentioned above,which possess the common property of dissolving in sodium sulfid with characteristic bottle-green color.
- thiocatechins are products insoluble in acids, soluble only in alkalies and alkaline suliids. On precipitating them from their solution in soda or sodium sulfid by dilute acid there is obtained a paste which in contact with alkaline sulfites or bisulfites becomes soluble and may be used in this condition or after drying directly for dyeing or with addition of a thickener for printing.
- the coloring-matters known as thiecateehins derived from aeetylated paradiamins in the manner herein set forth, said coloringqnatters dyeing unmordanted cotton in tints varyingfrom yellow to brown ,being soluble in water and alkaline solution, insoluble in acids and characterized by dissolving brown in alkaline sulfids.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
UNITED. STATES PATENT OFFICE.
ALOIDE FRANCOIS POIRRIER, OF PARIS, FRANCE.
SULFURETED DYE.
SPECIFICATION forming part of Letters Patent No. 561,276, dated June 2, 1896.
Application filed March 21, 1895. Serial No- 542,694. (No specimens.) Patented in France June 30, 1894, No. 239,714.
To all whom it may concern.-
Be itknown that I, ALCIDE FRANQOIS POIR- RIER, of Paris, France, have invented certain new and useful Improvements in the Manufacture of Coloring-Matters termed Thiocatechines, which improvements are described in the following specification, and for which I have obtained French Patent No. 239,714, dated June 30, 1894.
It is known that by the action of sulfur alone or of sulfur and caustic alkalies on simple or complex organic substances a certain number of coloring-matters are obtained. Among them the coloring-matters described in the specification of English Patent No. 1,489 of 1893, denoted by the generic name cachou de Laval, are obtained by causing sulfur and caustic soda to react on organic bodies of simple or complex character, such as sawdust, bran, wool, pyrogallol, and certain organic acids. Kopp has obtained (see Berichte, VII, 174G) coloring-matters of the same nature by heating dry acetate of soda with sulfur to a very high temperature.
In United States Patents Nos. 532,484 and 532,503, granted January 15, 1895, the same use of sulfur and caustic soda is disclosed and the same condition or reaction, but applied to aromatic combinations of known properties, such as dioxybenzenes, paradiamins, or amidophenols. The coloring-matters obtained in those three cases have the same reactions, the same characters, and are capable of the same applications. They differ only in the tints which they produce on vegetable fibers. NVhile cachou de Laval dyes gray brown, the coloringmatters of the United States patents referred to dye black and blue. Further, it is known that if sulfur alone is heated with aromatic monanims such as paratoluidin or alpha-metaxylidin, in which is a group CH para in relation to the amido group-basic matters are obtained capable of dying unmordanted cotton yellow tints. (See Berz'chte, XXII, 330, 422, 968.) These bodies, the nature of which is now well settled, are termed primulins, dehydrothiotoluidin, dehydrothio Xylidin, &c. Finally, it is also known that by heating, under certain conditions, hydrosulfate of ammonia, with substituted aromatic diamins, such as paraphenylenediamin dimethylated, a blue coloring-matter, methylin blue, has been obtained according to the German Patent No. 18,57 9. On the other hand, Ihave found that by making sulfur, or preferably sulfur and caustic soda or alkaline sulfids, react on these same paradiamins, simple or acetylated, under special conditions as to fusion and the state of the reagents which are together, there are obtained new coloring-matters very different from those above referred to, in respect not only of their chemical properties but also of the tints which they produce on fibers. They dye unmordanted cotton in tints varying from yellow to brown or red yellow, having remarkable luster and fast against various chemical agents. The following examples illustrate the process for their preparation.
Example I: I heat to 200 to 250 centigrade for three hours one hundred kilos acetyl-paraphenylenediamin and two hundred kilos sulfur. There shortly occurs a Violent reaction and evolution of sulfureted hydrogen, on the cessation of which the material is left to cool. The coloring-matter obtained is soluble in hot alkaline sulfids, and in this condition directly dyes cotton a brown yellow.
Example II: I heat to about 300 centigrade for three to four hours one hundred kilos diacetyldiazobenzidin, one hundred kilos dry sodium sulfite, and two hundred kilos sulfur. Then the reaction is complete, the material is allowed to cool and can in this conditon be applied to use. The coloring-matter, which is readily soluble in water, dyes cotton yellow.
Analogous coloring-matters may be prepared by heating under like conditions acetylparanitranilin, the nitrotoluidins and nitroalpha-naphthylamin, acetylated, or the corresponding amido derivatives. All these coloring-matters have the same properties. They are soluble in water, in alkaline sulfids, sulfites, and bisulfites, insoluble in acids. It is known, on the other hand, that the primulins and dehyrothiotoluidins or Xylidins are basic bodies insoluble in alkalies.
The combination of the new products with alkaline bisulfites has little stability, and even at 100 centigrade it reproduces the primary material. The solutions in alkaline sulfids are brown, thus differing essentially from cachou de laval and also from the coloring matters of the United States patents mentioned above,which possess the common property of dissolving in sodium sulfid with characteristic bottle-green color.
The ordinaryreducing agents do not attack the new coloring-matters. It is only at boiling-point that ZlIIC powder discolors the alkaline solutions by oxidation or reproduces the primary coloring-matter. Finally, has been shown,vegetable fibers are dyed directly in fast tints, yellow, brown, and red yellow. It is necessary to pass the material through an oxidizing bath (bichromate, iron perchlorid, or alkaline hypochlorite) in order to brighten the tints and definitely fix the dyes.
The eoloringmatters obtained as above set forth and which are termed thiocatechins are products insoluble in acids, soluble only in alkalies and alkaline suliids. On precipitating them from their solution in soda or sodium sulfid by dilute acid there is obtained a paste which in contact with alkaline sulfites or bisulfites becomes soluble and may be used in this condition or after drying directly for dyeing or with addition of a thickener for printing.
Example: The coloring-matter obtained by heating amidoacetanilid with sodium sulfid and sulfur is dissolved in hot water and precipitated by dilute hydrochloric acid. The precipitated coloring-matter is filtered and washed with a little acidulated water. To the paste are then added four parts crystallized sulfite of soda for each one part of the dry product, and the whole is intimately mixed. This mixture is heated to 30 to For the sulfitc of soda an equivalent quantity of bisulfite may be substituted.
\Vhere mention is made in the following claims of a single substance, it is to be understood that the equivalents thereof are in eluded. Thus where heating with sulfur is mentioned the intention is to include not only the use of sulfur alone, but the alternative process of using sulfur with alkaline sulfids.
Having thus described my invention, what I claim is 1. The described process of preparing co]- oring-matters which dye unmordanted cotton in tints varying from yellow to brown and red brown, by heating to the prescribed temperatures, with sulfur or sulfur compounds, acetylated paradiamins, as herein set forth.
2. The described process of preparing coloring-matters which dye unmordanted cotton. in tints varying from yellow to brown and red brown, by heatin g to the prescribed temperatures, with suli'ur or sulfur compounds, acetylated paradiamins, andv acting on the product of this reaction with sodium sullite, as herein set forth.
3. The coloring-matters known as thiecateehins, derived from aeetylated paradiamins in the manner herein set forth, said coloringqnatters dyeing unmordanted cotton in tints varyingfrom yellow to brown ,being soluble in water and alkaline solution, insoluble in acids and characterized by dissolving brown in alkaline sulfids.
In witness whereof I have hereunto signed my name in the presence of two subscribing witnesses.
A'LGIDE FRANQOIS POIRRJER.
\Vitn esses:
JoLEs AnMnNoAUn, Jeune,
CLYDE Snnorsrnnn.
Publications (1)
Publication Number | Publication Date |
---|---|
US561276A true US561276A (en) | 1896-06-02 |
Family
ID=2629998
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US561276D Expired - Lifetime US561276A (en) | Alcide frangois poirrier |
Country Status (1)
Country | Link |
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US (1) | US561276A (en) |
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0
- US US561276D patent/US561276A/en not_active Expired - Lifetime
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